Chapter 14, Problem 14.55P

Reaction of ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CH}}_{\text{2}}{\text{CH}}_{\text{2}}\text{OH}$ with ${\text{CH}}_{\text{3}}\text{COCl}$ affords compound W, which has molecular formula

${\text{C}}_{\text{10}}{\text{H}}_{\text{12}}{\text{O}}_{\text{2}}$. W shows prominent IR absorptions at $3088-289{\text{7, 1740, and 1606 cm}}^{-1}$. W exhibits the

following signals in its ${}^{\text{1}}\text{H}$ NMR spectrum:

$\text{2}\text{.02}\left(\text{singlet}\right)\text{, 2}\text{.91}\left(\text{triplet}\right)\text{, 4}\text{.25}\left(\text{triplet}\right)\text{, and 7}\text{.2}0-7.35\left(\text{multiplet}\right)\text{ppm}$. What is the structure of W?

We will learn about this reaction in Chapter 22.